The genus Cinnamomum

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Chemistry of Cinnamon and Cassia 97 There is no evidence, however, that these monoterpenes that occur in the cinnamon are synthesised in an analogous fashion. Biosynthesis of the sesquiterpenoids In cinnamon leaf, stem bark and root bark oils sesquiterpenes occur to an extent of about 4 to 5%. -caryophyllene and -humulene are the major sesquiterpenes, and together they contribute about 3 to 4%. Like monoterpenes, sesquiterpenes may occur in acyclic, monocyclic, bicyclic and tricyclic forms. Ruzicka’s biogenetic isoprenoid rule (1953) also applies to sesquiterpenes. Most of these terpenoids can be divided into three isoprene units connected head-to-tail, and thus the molecular formula is C 15H 24. Parker et al. (1967) proposed that the trans-farnesyl pyrophosphate (FPP) is the fundamental starting unit for the formation of sesquiterpenes. Like monoterpenes, sesquiterpenes occur in plant as hydrocarbons with functional groups such as hydroxyl and aldehyde. Farnesol is widely distributed in the plant kingdom (Simonsen and Barton, 1952). Since farnesol is formed by the union of three isoprene units, it follows that MVA should be a precursor of farnesol, in particular, and sesquiterpenes, in general. Many workers have reported the formation of farnesol from MVA. In particular Loomis (1967), Nicholas (1967), Rogers et al. (1968), Banthorpe and Wirz-Justice (1969), Staby et al. etc. (1973) have investigated both the formation and sites of sesquiterpene synthesis. Even though the incorporation of MVA into monoterpenes is less than 1%, the observed incorporation into sesquiterpenes was in the range of 2–4% of the fed MVA. Rogers et al. (1968) pointed out that mono- and sesquiterpenes are synthesised at different sites, which could account for the later incorporation of label into sesquiterpenes. They have suggested that sesquiterpenes may be synthesised outside the chloroplast, where applied precursors are more accessible. Mass Spectrometric Studies A systematic study of the chemical composition of Sri Lankan produced spice oils and essential oils was carried out by Mubarak and Paranagama (Paranagama, M.Phil. thesis, 1991). In this study these researchers used GC-MS techniques with capillary columns to investigate inter alia the essential oils of cinnamon, (leaf oil, bark oil and root bark oil). The essential oils were laboratory distilled from material derived from commercial sources. The authors also analysed the volatile oil of the cinnamon fruits for the first time (Tables 3.5 and 3.6). The constituents identified by these workers are listed in Table 3.6. The GLC patterns of fruit and root bark oils on carbowax 20 M capillary columns are given in Fig. 3.6 and Fig. 3.7. The and cadinenes (36%) are major constituents of the cinnamon fruits which have an array of compounds not found in the other sites explored. The fruits have relatively minor amounts of cinnamaldehyde and eugenol. Other compounds in the fruit volatile oil were cadinol T (7.7%), -caryophyllene (5.6%), -muurolene (4.4%), -cadinene (2.8%), -ylangene (2.7%) and -gurjugene (2.3%). The oil contained 67% sesquiterpene hydrocarbons, 17% sesquiterpene alcohols and only 1% phenyl propanoids. The aroma of the fruit therefore defers considerably from that of the leaf or bark, due to the sesquiterpenoids.
Table 3.5 Constituents of cinnamon bark, leaf, root and fruit oils, SPB-1 column Component % % % C. bark C. leaf C. root C. fruit Unknown – – 0.03 – -Pinene 3.34 0.73 5.70 2.19 -Thujene 1.10 0.08 0.57 – Camphene 0.63 0.29 2.77 0.29 -Pinene 0.61 0.26 3.45 1.61 Sabinene 0.26 – 1.51 – -Phellandrene 0.14 0.65 4.92 0.43 Myrcene 2.70 0.77 0.43 – -Terpinene 1.30 1.10 1.05 0.08 Limonene 1.21 0.32 6.16 1.00 -Phellandrene – – 2.09 0.07 cis-Ocimene 0.14 – 0.28 0.03 -Terpinene 0.16 – 0.57 0.05 trans-Ocimene 0.13 – 0.94 0.02 p-Cymene 1.91 0.92 1.38 0.01 Terpinolene 0.21 0.61 0.47 0.30 Linalool 3.70 2.77 0.13 0.08 -Terpineol – 0.06 0.05 – Terpinen-4-o1 0.40 0.11 1.90 0.27 -Terpineol 0.70 0.28 3.94 0.64 Fenchyl alcohol – – – 0.41 Isoborneol 0.08 – 0.68 0.70 Sabinol – – 0.20 – 1,8-Cineole 4.60 0.51 6.39 0.05 Methyl chavicol – – 0.19 – Cumenol* – – 0.06 – Cinnamyl alcohol 0.16 0.09 0.12 – Phenyl ethyl alcohol 0.47 – – – Coumarin 0.36 – – – Benzaldehyde 0.61 0.14 – 0.50 Hydrocinnamaldehyde 0.80 0.12 0.09 – Cinnamaldehyde 46.70 2.81 0.41 0.29 Camphor – – 47.42 – Piperitone* – – 0.24 – Phenyl ethyl acetate 0.18 – 0.05 – Phenyl prophyl acetate 0.38 – 0.03 – Methyl cinnamate 0.27 0.09 0.10 – Cinnamyl acetate 8.78 1.00 0.12 0.10 Benzyl benzoate 1.10 6.01 0.16 – Eugenyl acetate 0.40 0.64 0.10 1.00 Linalyl acetate – – 0.60 – Eugenol 4.15 76.74 0.21 0.45 Methyl isoeugenol – – – 0.22 Isoeugenol 0.08 0.07 0.04 – Safrole 0.08 0.08 1.32 0.32 Methyl eugenol 0.15 – 0.12 1.79 Methoxy eugenol – – 0.17 – -Cubebene – – 0.68 0.20 -Ylangene 0.70 0.14 0.03 2.71 -Caryophyllene 8.00 3.47 0.62 5.63 Sesquiterpene hydrocarbons – – – 0.50 Sesquiterpene hydrocarbon – – 0.08 1.41 Unknown – – – 0.30
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Cinnamon and Cassia The genus Cinna
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Cinnamon and Cassia The genus Cinna
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This volume is dedicated to Prof. (
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viii Contents 10 Pests and diseases
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x Contributors Subhan C. Nath Regio
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xii Preface to the series compounds
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xiv Preface When we approached the
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1 Introduction P.N. Ravindran and K
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French Casse, Canefice, Canelle de
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Introduction 5 were accomplished sa
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Introduction 7 It seems quite proba
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Introduction 9 rose to 450,000 kg.
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Introduction 11 Sri Lanka has been
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Introduction 13 ISO (1977) Oil of c
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Botany and Crop Improvement of Cinn
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(a) (c) Botany and Crop Improvement
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Indian cassia leaves (known as ‘T
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1 2 Botany and Crop Improvement of
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Table 2.4 Stomatal characteristics
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1 3 4 Collenchyma Stone cell Phloem
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Table 2.6 Microscopic characteristi
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(k) Medullary 2 cells wide, radiall
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1 7 1a 7 Wood anatomy 4 6 2 2a Bota
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(a) (b) Morning Botany and Crop I
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Page 66 and 67: Botany and Crop Improvement of Cinn
Page 78 and 79: viability is completely lost (Kanna
Page 82 and 83: Other tissue culture studies Botany
Page 84 and 85: Table 2.11 Bark and leaf oil consti
Page 86 and 87: Table 2.13 Growth and yield paramet
Page 90 and 91: Little crop improvement work has go
Page 98 and 99: Chemistry of Cinnamon and Cassia 81
Page 104 and 105: Table 3.4 Volatile constituents ide
Page 110 and 111: HO Chemistry of Cinnamon and Cassia
Page 116 and 117: -Humulene 1.30 0.57 0.12 1.40 -Cube
Page 118 and 119: 1 3 2 4 4 5 7 6 8 10 9 12 11 13 14
Page 120 and 121: 1147 Isoborneol 0.36 0.55 1158 Born
Page 124 and 125: opportunities lies in the new centu
Page 126 and 127: R OH 4 HO O O O OH Chemistry of Cin
Page 132 and 133: p-Cymene 13 21.35 0.82 -Copaene 0.4
Page 134 and 135: (E)-cinnamyl acetate 0.1 0.2-2.2 -3
Page 136 and 137: Annex 3.3 The chemical structure of
Page 138 and 139: 4 Cultivation and Management of Cin
Page 140 and 141: Figure 4.2 Field plantation of cinn
Page 142 and 143: the age of three to four months exc
Page 144 and 145: Cultivation and Management of Cinna
Page 146 and 147: Cultivation and Management of Cinna
Page 148 and 149: HARVESTED CINNAMON Cutting Extracti
Page 150 and 151: (a) (b) Figure 5.3 (a) Cinnamon pee
Page 152 and 153: Chips Harvesting, Processing, and Q
Page 154 and 155: cassia oils, is obtained from disti
Page 156 and 157: KETTLE FURNACE Harvesting, Processi
Page 158 and 159: the oleoresin is stored in suitable
Page 160 and 161: Grades The Cinnamon bark shall have
Page 162 and 163: Quality of Reagents Unless specifie
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Cinnamon powder Harvesting, Process
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Table 5A.5 Chemical requirements Ha
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Harvesting, Processing, and Quality
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Special protection information Resp
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Ash Refer to Annex 5.3. Acid insolu
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Chinese Cassia 157 Figure 6.1 Cinna
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Figure 6.2 A 15-year old plantation
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Chinese Cassia 161 careful harrowin
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make it easier to climb and to avoi
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Adulterations and substitutes In ea
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Chinese Cassia 167 various regions
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Table 6.4 Insect pests of cassia ci
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Chinese Cassia 171 Table 6.5 Compos
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Trace Methyl eugenol Trace Benzoic
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Table 6.9 Comparative percentages,
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Chinese Cassia 177 (3-5°C) or due
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Chinese Cassia 179 curing diseases
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Chinese Cassia 181 different parts
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Chinese Cassia 183 Kashiwada, Y., N
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7 Indonesian Cassia (Indonesian Cin
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propagation is possible through cut
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Indonesian Cassia (Indonesian Cinna
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Figure 7.3 Separation of bark by be
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the branch. The mycelium layer pene
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Table 7.4 The yield and characteris
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Conclusion In spite of the fact tha
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8 Indian Cassia Akhil Baruah and Su
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Indian Cassia 201 pollen dehiscence
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Indian Cassia 203 Ecology and distr
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Table 8.1 Physico-chemical characte
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Indian Cassia 207 Table 8.4 Composi
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References Indian Cassia 209 Anonym
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9 Camphor Tree K. Nirmal Babu, P.N.
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Sub-specific division of C. camphor
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Camphor Tree 215 succession species
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The condenser is the most bulky and
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Table 9.1 Relation between age of t
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Table 9.3 Yield of camphor and oil
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Camphor Tree 223 Yu-Sho oil: Specif
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Ketones and oxides: Camphor, piperi
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Camphor Tree 227 20 Citronellyl ace
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Table 9.12 Chemical composition (%)
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Camphor Tree 231 Table 9.14 Yield a
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Camphor Tree 233 Table 9.18 Physico
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Camphor Tree 235 To prevent bed-sor
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Camphor Tree 237 Chopra, R.N., Chop
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10 Pests and Diseases of Cinnamon a
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Family: Dermestidae Evorinea hirtel
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Pests and Diseases of Cinnamon and
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Leaf webber (Orthaga vitalis) Pests
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C. malabatrum Meliola beilschmiedia
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11 Pharmacology and Toxicology of C
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Anti-inflammatory action Pharmacolo
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Pharmacology and Toxicology of Cinn
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Table 11.1 Antibacterial effects of
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Table 11.2 Antifungal activity of c
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12 Economics and Marketing of Cinna
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Economics and Marketing of Cinnamon
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Table 12.7 US imports of whole cass
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Japan Economics and Marketing of Ci
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Table 12.14 US exports of cassia an
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Table 12.16 World exports of cinnam
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Table 12.20 US imports of cassia oi
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S t 0.37Y t 0.63S t1 Economics an
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13 End Uses of Cinnamon and Cassia
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Table 13.3 Typical western pickling
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End Uses of Cinnamon and Cassia 315
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Table 13.9 Relative flavour intensi
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Cinnamon - in perfumes and beauty c
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Chinese Cassia Chinese cassia - as
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14 Cinnamon and Cassia - The Future
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Cinnamon and Cassia - The Future Vi
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Table 15.1 Chemical composition of
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Table 15.3 Constituents of leaf oil
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cloves. Leaves measure 3-12 1.5-4
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C. deschampsii Gamble C. deschampsi
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Table 15.7 Composition of essential
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Other Useful Species of Cinnamomum
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Table 15.9 Compounds identified in
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C. sulphuratum Nees Other Useful Sp
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Table 15.13 Percentage composition
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location 90 physico-chemical proper
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mass spectrometric studies 97 extra
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metabolic studies 267 sedative effe
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The genus Cinnamomum

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